Solvent-Free Alcoholysis of Tripalmitin to Produce 2-Monoglyceride as Precursor for 1, 3-Oleoyl-2-Palmitoylglycerol
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2-monoglyceride (2-MAG) was essential to produce high purity of 1, 3-Oleoyl-2-palmitoylglycerol (OPO), an important infant formula additive. Traditional synthesis of 2-MAG requires chemical solvent to solve the high melting point substrate, yielding the risk of solvent residue in OPO. This paper developed a solvent-free synthesis route of 2-MAG by alcoholysis of high melting point tripalmitin (PPP). Ethyl palmitate (EP), one of the reaction byproducts, was added in the beginning of alcoholysis process to promote the solubleness of high melting point PPP, avoiding the addition of toxic chemical solvent. The product of alcoholysis was separated by two-step molecular distillations. Separated DAG was used to produce 2-MAG and the final conversion of 2-MAG reached about 85.90%, with the purity of 92.36%. 2-MAG was trans-esterified to OPO with ethyl oleate, and the yield of OPO was up to 85.06% with 80.17% palmitic acid located on sn-2 position. The solvent-free synthesis route avoids the usage of hazardous chemical solvents, providing safer infant formula additive.
KeywordsCandida sp. 99-125 Alcoholysis 2-monoglyceride Monopalmitin Solvent-free synthesis 1, 3-Oleoyl-2-palmitoylglycerol
This research was financially supported by the National Key R&D Program of China (No. 2017YFD0400603), the Innovation Fund for Technology Based Firms (No. 14C26213511838), and the National Key Research Development Program (No. 2016YFD0400601).
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Conflict of Interest
The authors declare that they have no conflicts of interest.
- 7.Esteban, L., Jiménez, M. J., Hita, E., González, P. A., Martín, L., & Robles, A. (2011). Production of structured triacylglycerols rich in palmitic acid at sn-2 position and oleic acid at sn-1,3 positions as human milk fat substitutes by enzymatic acidolysis. Biochemical Engineering Journal, 54(1), 62–69.CrossRefGoogle Scholar
- 8.Zhang, X., Nie, K., Zheng, Y., et al. (2016). Candida sp. 99-125Coupled with β-cyclodextrin as additive synthesized the human milk fat substitutes. Journal of Molecular Catalysis B: Enzymatic, 2125, 2011–2015.Google Scholar
- 23.Liu, C., Yan, Z., Xin, Z., Nie, K., Li, D. and Fang, W. (2016). The two-step synthesis of 1, 3-oleoyl-2-palmitoylglycerol by Candida sp. 99-125 lipase. Journal of Molecular Catalysis B Enzymatic, 133 , S1381117716301989.Google Scholar